Trial And Error
by tfdias
Summary: AU: Best friends Olivia and Fitz work for an online popular culture blog and seek out a new adventure when they team up together for Olivia's new blog project. Some humor and guaranteed smut! Rated M for content and language.
1. The 'Super Duper'

"Morning everyone!"

She walked into the office, cheerful and relaxed, carrying a cup of her favorite Starbucks drink - a venti soymilk peppermint mocha frappuccino. Her heels clacked on the building's black and white marble floors as she made her way to her office. She waved at Quinn, smiled at Huck, and poked her head into Abby's office, all before swiping her card to open her office door. She placed her cup on a coaster, removing her Michael Kors travel tote from her shoulder, setting it on the round wooden table in the corner. She stood on her tip toes as she reached over the table, pulling to blinds open to let in some light. The bright Miami sun shone in through the room, and she momentarily enjoyed the beautiful view of the ocean, before a light tapping on her door caught her attention.

"Mornin' sunshine", he said, leaning on the door frame with his arms crossed; a huge smile spread across his face. That smile. Jesus. It never ceased to amaze her.

"Morning Fitz", she responded, waltzing across the room to give her coworker and long time best friend a hug.

"I see you had a lovely weekend Liv", he entered into the room, closing the door behind him.

"I sure did. Did some light shopping and the beach Saturday and I enjoyed a little spa visit yesterday afternoon. The perfect way to bring in the new year. I feel so refreshed and energized, nothing can ruin my mood."

"Oh, I have a feeling that's about to change. Swedelson pushed up the 'super duper' to this afternoon. So, unless you were prepared to present your idea today instead of as originally intended next week...", his voice trails off.

"Shit! Are you kidding me! I haven't thought of shit! I wasn't expecting to have to present until next week. When the hell did this happen?"

"I guess while you were out shopping, beaching, and spa-ing, you didn't check your e-mails this weekend?"

"I'm so screwed!"

* * *

Olivia sat nervously at the conference table, tapping her fingernails on the wooden surface. It was PopuBlog's 2014 "Super Duper", the annual meeting where each of the online blog's contributors laid out their ideas of focus for the year. Mr. Swedelson, the founder of the blog, sifted through all of his employees' ideas, either praising them or turning them down and "sending them back to the drawing board". It was a known fact by all of them that if you were unable to produce a worthy idea during the "Super Duper", you would be despised by the "Big Guy" for the rest of the year.

Olivia's mind tried to draw up different topics that she could possibly focus on for the year, while everyone went around the table laying their ideas on the line. Last year, she had done a challenge where she would cook at least one reciepe from each of the 196 countries in the world. Her idea had done well, not only for the blog, but in the building as well, where she would bring in samples for everyone to try. She listened as Fitz discussed his idea for the year; two separate video blogs (one for guys, one for girls) where they would discuss different gender-oriented topics. Swedelson ate up his idea, prompting Fitz to lean back in his chair, a huge smile on his face.

_"Good! He's on the other side of the table! I still have a few minutes!"_, she thought to herself, while the ringer on her cellphone went off, bringing all of the attention in the room to her direction as she shuffled in her purse to find it.

_"Seriously?!"_, she scolded herself in her head for forgetting to silence her phone when she realized it was a notification from the"Cosmopolitan's Sex Position of the Day" app. She quickly threw her phone back in her purse and looked up to find Mr. Swedelson glaring at her.

"Well, Ms. Pope, it seems that we're boring you and there must be something you much rather be doing. How about you give us your idea next?", his British accent filled the silent room.

"Uhh...", she stuttered to herself, knowing she had nothing and she didn't want to feel his wrath for the rest of the year for coming to the meeting unprepared. She quickly surveyed the room, looking at Quinn, Abby, and Huck who all smiled at her nervously. She then focused her gaze on Fitz, who was looking back at her with a raised eyebrow.

"Ms. Pope, we're waiting..."

"Umm... a sex blog!", she blurted out, causing everyone to look at her like she was crazy.

"Excuse me, Ms. Pope?"

"You know how Cosmopolitan magazine features sexual advice? Well, umm, they have this app... phone app, that gives you new positions everyday...", she figured she could keep going with the idea since it was already on the table.

Mr. Swedelson stared at her for what seemed like an eternity, before he asked, "So, you will be testing out a new...", he cleared his throat, "...sexual position every day from this little app thingy?"

Shit. She hadn't thought about that. But, he seemed interested in her idea and she thought it wouldn't hurt to give it a shot.

"Yes sir."

"And I assume these... positions... will be acted out with one consecutive partner?"

"Yes sir", she gulped nervously. _"Who the hell am I supposed to sleep with everyday for the next year? Maybe this idea wasn't so great after all..."_

"Ms. Pope, it seems you've brought forth a fantastic idea, again. What would be your medium for this project?"

"Umm.. text posts, sir. Basically rating and discussing the experience..."

"Well, I expect for you to discuss with Huck on how to make sure your section of the site will be aged-restricted. I also expect a copy of a negative STD screening result from both you and your partner before you can start your project. Or, it'll be back to the drawing board. I assume that this partner will stay anonymous?"

"Yes sir!", she answered a little too loudly. She was off the hook for presenting an idea that was accepted by the "Big Guy", but now she was screwed when it came to figuring out how she was going to make it happen.

"Let's continue, shall we. Ms. Perkins?"

* * *

Olivia and Fitz sat at the bar, enjoying well-deserved drinks after a long day at work. They had taken a few shots of Patron each, before Fitz ordered a glass of scotch and Olivia ordered a frozen strawberry margarita. They were both well passed tipsy, but hadn't reach stumbling drunk yet.

"Fitz, I'm seriously gonna get killed. He's definitely gonna send me back to the drawing board."

"Where'd you come from with that idea anyways? I thought you didn't have anything..."

"I didn't! It was the freaking sex app that went off in the meeting and it was the first thing I could think of on the spot!"

"Liv, why do you even have a sex app? You're not screwing anyone! What, does it have positions on how to screw yourself?", he laughed as she shoved him hard, nearly knocking him off of the bar stool.

"It's a cute app! And it's cool to know these things for when I AM gonna be screwing someone. You asshole!", she rolled her eyes. "But really Fitz, I need your help. What am I gonna do? How do you scrap an idea that Swedelson actually likes?!"

"You're fucked Liv. Seriously fucked. And it sucks because you're not getting any pleasure out of if. I wish I would have thought of it first. It's nothing to find a chick to fuck every night when you have this gorgeous face", he winked at her. "Hell, you'd probably be better off just screwing me", he took another sip of his drink.

"Fitz! That's it! You're fucking brilliant!"

"What's brilliant?", he asked, clearly forgetting with they were speaking about just moments ago.

"Be my guy Fitz! Be my partner!"

"Olivia, are you out of your mind?", he said with all seriousness.

"Come on Fitz, think about it. I'm single, you're single. We've been best friends since like forever. I've seen you naked!", she shouted out as the bartender approached them, planning to ask if they wanted refills, but then turned to walk away awkwardly.

"Olivia! Keep it down will you! And seriously? Me? You? US? Having sex?"

"Fitz, it's not like I'm asking you to marry me. Just help me! Think of it as us both just experimenting, both of us learning. We both know each other and we both know how to play it safe. PLUS, Swedelson said that it has to be an anonymous partner. No one will ever know it's you! Please Fitz, please?! I wouldn't ask if I weren't absolutely desperate..."

He thought about it for a minute, seeing the look of desperation in her eyes. He thought she was absolutely crazy for suggesting something so wild, regardless if they were friends or not. But Olivia was his truest friend and had always been. He knew she needed his help and he honesty saw more pros than cons.

"Okay, fine. I'll do it. But the moment it gets really weird, we gotta stop. I don't wanna fuck up our friendship over some project Liv, you hear me?"

"Absolutely! Now, we just have to get tested and give the Big Guy the results."

"Whatever, let's go", he hopped off the stool, pulling a $100 bill from his wallet and placing it on the counter to pay for their drinks.

"Where are we going?", she asked him confused.

"Back to your place. I wanna see this app..."

* * *

**AN: Hey guys! So this is an idea I recently began playing with. It was one that I've never seen done before, so I decided to try it. Just want to cover a few things. Firstly, Cosmo's sex app is a real thing. Do I own it, NO! Why pay for an app when all of their stuff is free online! Secondly, some aspects of this story might seem a bit familiar. For one, the idea of Olivia blogging about a new recipe comes from the movie (and I believe book, as well), called Julie & Julia. Great movie, if you've never seen it, and it stars Meryl Streep, who I absolutely love! Then, Fitz's idea for a video blog comes from MTV's Girl Code and Guy Code. Both are hilarious shows that give insight on things from girls' and guys' perspectives. And lastly, Olivia's idea to blog about the sex positions featured in Cosmo comes from the "77 Positions In 77 Days" feature from Cosmo. I actually read it online a few years ago while the blogger was updating it daily and it's seriously an interesting and funny read. So, I just wanna let you guys know that by no means am I stealing these ideas. I also wanted to say that I'm not sure if every chapter of the story will connect, or if it'll just be one shots of the different positions. AND I'm not sure if there will be some sort of Olitz love connection, or if they will continue on as just friends. So, please please please let me know what you guys think! Think of it as you guys being the Mr. Swedelson to my Olivia lol (:**


	2. Rules and Regulations

"Wow. I can't believe someone actually tried out this position and didn't die..."

"What are you looking at?", she walked over to her couch, taking a seat next to him.

"Look!", he moved the laptop to sit on both of their laps, pointing at a picture on the screen. The both of them tilted their heads to get a better look at the picture, a look of disgust flashing across both of their faces.

"Oh... we're definitely not trying that one. At all. Ever."

"Ever!", he agreed. "Liv, how is this supposed to work anyways?"

"What do you mean?"

"Like... how do we not make this weird? What can and can't we do? What should we be doing?"

"Fitz, I'm confused...", she straightened herself as she turned towards him. _"Please don't tell me he's chickening out..."_

"I mean... are we supposed to kiss? Do we undress each other or do we undress ourselves? Are we supposed to enjoy it? Like... what are we supposed to do?"

"Hmm...", she tapped her fingers to her chin as she pondered for a moment. "I don't know. I mean, I didn't really think about it. Maybe we should have rules? Yes, we should definitely have rules...", she popped out of her seat and grabbed her iPad from it's charger in her office before returning to join him in the living room. "Any suggestions?"

"You go first.."

"Well, safety is definitely a must."

"Condoms?"

"Yeah.."

"Are you still on the pill?", he asked, knowing that she had been on birth control, as he had had to pick up her prescription from the pharmacy a few times in the past years. "You know, in case of emergency...", he said quickly when he noticed her staring at him with a raised eyebrow.

"Yeah... should I be buying your condoms, or..."

"Don't worry about it... should there be like... foreplay?"

"Foreplay? I think it'll make it a bit awkward.."

"It's already gonna be awkward Liv..."

"Shut up! Next question?"

"How are we gonna pick positions? I mean, I think you should definitely pick. This is your project. I'm just your sex slave for the next year..", he laughed.

"You're so not!", she joined in his laughter. "You should have a say too! Don't you think?"

"I wouldn't mind…"

"Okay, how about this.. I'll give you the honors of picking the first one and whoever 'finishes' second gets to pick the next one…"

"Liv..", he raised an eyebrow as he watched a smug smile spread across he face. "Are you saying that if I make you come first, I get to pick the next position?"

"Yes. I doubt that'll ever happen, but fair is fair…"

"You're full of shit!", her tickled her, causing her to scream out in laughter.

"Okay okay! I'm sorry! I was joking! But it's a pretty decent rule."

"It is. Is there anything off limits for you?"

"Nothing dangerous. Nothing that will cause either of us bodily harm. And nothing anal.."

"Anal? Seriously Liv? You think I would.."

"Hey! I don't know what you're in to!"

"Not that. Well, I wouldn't know, but…"

"Anyways…", she tried to change the subject, "Anything off limits for you?"

"Nope. Just nothing too weird. How is this supposed to go with relationships?"

"Relationships?", she asked a bit confused.

"I mean, should we stay single, or…"

"Or…"

"I'm not really sure I'd be able to explain to someone that I'm sleeping with my friend for a project for work. AND adding someone else to the mix could definitely bring along risk for diseases."

"Fitzgerald Grant, are you saying that you, Mr. Hot Stuff that switches women like underwear, are willing to give up relationships AND commit to me and only me sexually for a whole entire year?", she questioned him mockingly.

"Cut the crap Liv! You know I'm not a player! I just like to explore my options.", he ducked as she threw one of the decorative pillows on the couch at him. "And honestly, a year couldn't be that bad. At least I have you all to myself…", he grinned at her, causing her to blush.

They had been friends since they were in diapers, growing up living next door to one another. Her parents, Maya and Rowan Pope, raised their daughter on a combined salary as a elementary school teacher and a heart surgeon, respectively. His parents, Elaine and Fitzgerald Grant II, were both therapists. Their parents were all good friends, spending lots of holidays, game nights, and special occasions with one another.

Both were only children. Fitz had often escaped to the Pope household when his parents had began to drive him crazy with their psychological views on just about everything when it came to raising him. Olivia would often have dinner with the Grants when her mother was away at educational seminars and her father had to attend to unexpected surgeries. They were the same age, Fitz only a few months older, and they were basically inseparable since birth.

They attended the same schools and had been classmates a few times. Together, they dominated their schools, especially when it came to high school. They were both very popular, using their social status to help influence their peers to raise money for fundraisers and volunteer in community service projects. They challenged each other academically, Olivia eventually being named their high school valedictorian, with Fitz ranking in place right behind her. But, they both took home a crown after their senior prom.

They eventually left home and attended the same college, sharing an apartment together with Fitz studying film and Olivia studying writing. They came to each other with all of their relationship issues, Fitz usually wiping away the tears and indulging in a night of Ben & Jerry's when Olivia ended up heartbroken and Olivia usually having to find out all of the information on whichever new girl Fitz seemed to be interested in. They shared an overwhelmingly close bond, but they had always been platonic. They were basically soul mates in friendship form. Knowing so much about one another made this arrangement so much easier; they were confident Olivia's project could be completed without any issues.

"Okay loverboy, let's not make this anymore weirder than it already is. So here's how this is gonna work…"

They sat discussing how everything would work, making it comfortable for the both of them while still ensuring that Olivia was able to end up with a great product. They decided that it would be best for Fitz to remain completely anonymous, to both readers and their coworkers and friends. They would both write about their experience with the position they tried: what they liked or disliked about it, where they felt the most stimulation and any alternatives. Then, they would give it a rating, which ranged from 0 to 5 stars.

They would try to do 365 positions throughout the whole year. Fitz figured it would be a good idea for them to start off using one position, then gradually adding more, so they could complete their goal in time, factoring in the days that Olivia would have her monthly or they just weren't in the mood.

"Music?"

"Pandora."

"Fitz, do you really think I wanna hear someone blabbing about some technical school in the middle of me getting on my swerve on?"

"The 'swerve' will be so great, you won't even notice the commercials."

"Get outta here!", she giggled, leading him over to the front door, "I'll see you for our appointment in the morning and DON'T be late!"

After a long week of them waiting to hear back from the doctor's office, the both of them receiving negative test results; having Huck set up an age-restricted section of the site and Olivia compiling a long list of positions that they could choose from, Mr. Swedelson had given her green light to finally begin her project.

* * *

**AN: The feedback for the first chapter was amazing! I'm really glad you all enjoyed this idea and I'm definitely excited about writing it. It took me some time because I haven't been in much of a mood of writing lately, BUT I've had majority of this chapter written from before I even posted the first one. So, it is a bit short because I was so out of it towards the end lol. Majority of you guys chose for there to be some Olitz action in this story, and to not base it off one shots, which I definitely have no problem with. The smut is definitely coming next chapter and you are all free to request/suggest positions that should be used! I plan to update this, as well as Rescue Me and Oliver & Company whenever I get my mojo back, so hang tight!  
**


	3. Let's Do This

**AN: I know it's been some time now since my last update (all on my stories), but I've been super busy. I've had updates written most of the way for all of my stories, but I just haven't found the time or the muse to complete them all. This might be a bit short, but I found myself grasping for words and they were not coming to me at all. Anyways, hope you all enjoy!**

* * *

Olivia paced the floor of her living room nervously. She fluffed and refluffed the couch cushions, turned the candy bowl sitting on her coffee table before walking by it and turning it again, and kept looking out of the peephole in the front door in anticipation. She had changed her outfit about four times, before she finally settled on a pair of old gray sweats and an old college football jersey. She had spent much too long in front of the mirror, deciding on how she wanted to wear her hair; first letting her curls frame her face, then gathering her hair and letting it all cascade down her left shoulder and lastly twisting it up in a messy bun, securing it with a ballpoint pen. "What am I doing? It's only Fitz!", she chastised herself for trying to put so much into her appearance.

"Where the hell is he?", she asked herself after she looked at her watch and noticed that he was about fifteen minutes late. After getting the go ahead from Mr. Swedelson, they had both decided to meet up that Friday night after work around 8:00. It gave them both enough time to get home, shower, and get their nerves together before meeting at Olivia's house for a "practice run".

"He's not coming. He's never late for anything!", she angrily flopped herself on the couch. "What in the hell were you thinking Olivia, trying to sleep with your closest friend?!" As she continued to argue with herself, she heard a knock on her front door. It wasn't just any ordinary knock, it was a beat created with bangs that created a rhythm. She knew it could only be one person and she popped off of the couch, hurriedly reorganizing the cushions and checking herself out in the large mirror in the foyer before she swung open the door.

"Hi", he smiled at her.

"Hi", she responded, her face holding a relieved expression.

"I'm sorry I'm late. I had to make a quick run to the store, and I got you these", he pulled a bouquet of freshly cut roses out from behind him. "I hope you didn't think I stood you up or anything..."

"Roses?", she asked, ignoring his previous statement.

"Too cheesy?"

"They're beautiful, thanks Fitz.", she grabbed the bouquet from him and moved to the side, allowing him to enter her apartment.

"Excuse me while I go find a vase. Make yourself at home, you've been here enough", she walked away into the kitchen and he caught himself staring at the sway in her hips.

_"Has her ass always been that big?"_, he questioned himself, never really ever taking the time to check Olivia out. What he now noticed caught him by surprise. He shook his head, walking over to the kitchen, placing a bag on the island.

"What's all that?", she asked curiously as she set the vase down into the sink to fill it with water. She watched him as he began to reveal the contents in the bag.

"Condoms, lube, tissues, wipes, hand sanitizer..."

"What are you, some sex germaphobe?"

"Sex gets messy Liv, I just wanna be prepared...", he flashed a grin and she rolled her eyes.

"Whatever! What else you got in there?", she leaned over trying to take a peek into the bag as he pulled out the rest of the items.

"Ice cream and a DVD?"

"I figured we could order in and watch a movie after? Unless you had other plans or whatever...", he answered shyly and she could sense that he was just as nervous as she was. Her heart smiled at his thoughtfulness in wanting to spend time with her after, instead of just getting in, getting off, and getting out.

"Nope, no plans. A movie after will be fine..", she smiled at him, taking the huge carton of Blue Bell mint chocolate chip ice cream and bringing it into the kitchen.

"So, have you picked a position yet?", her voice loud as she tried to talk over the humming in the freezer.

"Yea...", he called out, grabbing a mint from the candy bowl on the coffee table, before taking a seat on the couch.

"So...", she walked over to him, iPad in hand as she took a seat next to him, pulling up the Cosmo webpage. "Which one is it?"

"This one!", he said after grabbing the tablet from her hands and scrolling and tapping on the screen a few times.

**"The Rock & Roll?"**, she looked over at the screen, reading the instructions and checking out the illustration. "A missionary position? What the hell are you tryna do? Hypnotize me with your dick?"

He laughed at her outburst and after calming himself down, he said, "No Liv. Missionary is easy. I figured we'd take it off slow, get to know each other's bodies and what not, before we start doing anything too complicated..."

_"God, he's so sweet. Has he always been this sweet?"_, she asked herself as she sat speechless.

"Umm, okay, I guess you're right", she finally spoke up. "So, I guess we can start?"

* * *

With the door locked and the both of them standing on opposite sides of Olivia's huge king sized bed, they both stared at each other, neither of them wanting to make the first move.

Fitz couldn't believe this was about to happen, that he was about to sleep with his best friend. He had never seen Olivia as anything more than a friend, but in that moment, something changed in him. He felt the room get hot instantly, like the walls were closing in on him. He felt his heart beating through his chest. Sure, he had seen Olivia in a bathing suit countless of times, even catching her in her bra or underwear while she quickly changed in front of him. But, to see her fully naked?

"So umm, how are we supposed to do this?", he asked first.

"I guess we can get undressed, right?"

"Yeah, sounds good..."

The both of them turned away from each other, shaking hands unbuttoning shirts and pulling down pants. Olivia swallowed hard, trying her hardest to catch her breath while she had these last few moments to herself. Mentally, she second guessed herself and wondered if she was making one of the biggest mistakes of her life. This was going to be a new level of intimacy that she was going to share with Fitz and for the first time since they both decided to go through with this, she was having a bit of regret. But, she couldn't back out and she definitely couldn't let him see her nerves taking over her.

Moments later, they turned back around to face one another, both taking in the sight before them. Fitz stood in front of her in a pair of Calvin Klein boxers. He had always been one well aware of his good looks and had always complemented them with the finest of brand names products that money could buy. She smiled to herself as she took in his appearance. _"Once a pretty boy, always a pretty boy.."_

Fitz tried to keep his eyes from wandering over her perfectly toned body. Her breasts slightly hanging as they were supported by baby blue padded bra. Her flat stomach adorned with the beginning signs of a forming six pack. Her curves extending to her thick thighs, her hips hidden behind the fabric of her baby blue underwear. _"Damn..."_, he thought to himself as he felt his arousal beginning to stir.

"Seriously Olivia?" he asked with a fake hint of annoyance. He needed a distraction for the both of them; he couldn't let her see the effect that she had on him, fearing that it would creep her out.

"What?", she seemed puzzled and shocked.

"Granny panties? Oh come on! I know you don't wear these on a hot date! Am I not good enough for pretty panties?!", he joked with her, helping to lighten to mood for the both of them. "I wore Klein for you!"

"Oh please Grant. I would never waste my best panties on the likes of you!", she shot back, a huge smile on her face.

"Ouch Liv, a shot straight through the heart!"

The both of them laughed, their nervousness starting to fade away. Whatever doubts they might of had instantly left the room and both of their spirits lightened. They were ready to do this, it was either now or never.

"Let's do this Grant."


	4. Rock & Roll

She took a deep breath as she dropped her arms and looked down to find her bra and panties pooled on the floor by her feet. She felt relief as the cool air circulating in the room came in contact with her body. She turned around to find Fitz with his back still towards her, his boxers pooled around his ankles. They had mutually decided that they would undress themselves and that Fitz would be allowed to take the lead in the night's activities. She found herself checking out his bare body; his broad and muscular back that slimmed down towards his waist, showing off his firm ass and defined legs. She had to admit, his body was amazing and it was no wonder why it was never hard for him to find his way in between some dumb slut's legs. She felt herself getting hot all over again, which took her by surprise.

"Ahem", she forcefully cleared her throat, alerting Fitz that she was ready to begin. She heard him take a deep, shaky sigh before he turned around and faced her. Immediately, her eyes headed south and she couldn't even fight the next words to come out of her mouth.

"Jesus Christ!", she screamed out.

"What?"

"Why is it SO damn big? Mission abort! That's not going anywhere near me!"

"Seriously? I'm not even hard yet..", he said with a serious face, causing Olivia's eyes to bulge and words to get caught in her throat. "I'm kidding!", he began laughing hysterically, and she moved to fold her arms across her chest.

"Fitz, couldn't you at LEAST have given me some kind of warning? I knew you bragged but I never thought you were that serious! You're gonna rip me inside out!"

They both enjoyed the moment of being completely naked in front of each other for the first time, mere minutes from having sex with one another, and still being able to joke around.

"I'll take it easy on you, I promise!", he chuckled as he crossed his heart. "You look pretty good, by the way", a devilish smirk spreading across his face.

"Whatever!", she countered back, sticking out her tongue at him.

"Get on the bed Liv.."

* * *

**_Choose any flat surface — the floor or a even a sturdy table — and lie faceup, bringing your knees as close to your chin as you can._**

Liv laid with her back flat against the bed as Fitz moved himself across the bed.

"Okay Livvie, I'm gonna move your legs the right way, okay?"

She nodded as he positioned himself on his knees on the bed in front of her. She watched as he carefully ripped the packaging to the condom, pinching the tip, and slowly rolling it down his length. She bit her bottom lip as she watched him handle his package, squeezing some of the lubrication in his hands before using it to coat his hardness. His hands began to shake slightly as he grabbed on to her ankles, slowly opening her legs. He involuntarily licked his lips as he watched her delicate flower spread for him, her moisture quite evident. Her scent filled his nostrils and he felt a chill run down his spine.

"Damn", he whispered, looking up to meet Olivia's eyes.

"What?", she asked when she noticed his piercing gaze.

"I know this is probably the most awkward time to say this, but you are so beautiful Olivia."

She blushed before thanking him and laying her head back against the pillow as he bent her knees, pushing her legs as far back as possible.

"Is this okay?", he asked out of concern, not only because he had her in the most awkward position physically, but also because she was in a very vulnerable position as well. "I mean, I'm not hurting you or anything right?"

"Everything's good", she answered quietly.

_**He lies on top of you, and while you rest your calves on his shoulders, your man should enter you just as he would in the missionary position.**_

"Ready?"

"Ready."

He positioned himself between her legs, throwing her calves over his shoulders as he moved himself towards her core. Slowly, he began to enter her, penetrating her with just the head. He took his time, allowing her to adjust to his size before he began to push himself deeper inside her.

"Fuck", they both moaned once he reached halfway. He couldn't believe how wet, how tight she was. He felt himself already about lose control and he hadn't even begun to move yet. She couldn't believe how thick, how hard he was. She was pretty sure he was nowhere close to being all the way inside of her, but she was already full to the brim.

He withdrew slowly, a hiss escaping her lips while he prepared to enter her again. "Livvie, am I hurting you?", he paused to ask her. Truthfully, it was a bit painful, but he felt too damn good for her to make him stop.

"Keep going", she groaned softly, the sound of her voice driving him crazy. He began bury himself deeper until his entire length was inside of her, his tip grazing against her spot. Her hands went to his stomach and he was scared that he was hurting her.

"Liv, do you need me to pull out some?"

"No, right there is good"

_**For some extra leverage, grab hold of his upper arms. He'll likely need to have his palms flat down for support as he begins thrusting inside you.**_

Her hands moved from her sides to his arms, her nails clutching to his skin. His hands lay flat against the sheets and he bit his lip as he started to stroke her slowly.

"Oh shit!", she moaned as he began thrusting. "Oh shit, oh shit, oh shit!" She couldn't control herself. She wanted to come out strong, not letting him have the upper hand in making her come first, but she felt herself losing grip. The combination of his size and the way her legs were pinned to his shoulder, causing him to reach depths that no man had ever gone before, was something lethal. Not to mention his stroke. He took his time, moving in and out of her at an extremely slow place and although she knew he was trying his best not to hurt her, he was damn near about to make her give up. With every stroke, he hit her spot perfectly. She could feel his thickness move along her walls and she couldn't fight the moans now escaping her lips.

Her moans filled the air and it was the sexiest thing he had ever heard. The combination of the sounds escaping her and the warmth between her legs had him ready to give in. He moved slow so that he wouldn't hurt her, but with every stroke, her walls clamped on to him tighter. He watched her breasts bounce slightly with each thrust and the way her body looked beneath him...

"Oh my god!", she whispered breathlessly, causing him to shift his attention from her stomach to her face. He watched as her face distorted while she bit her bottom lip and her eyes locked tight. He knew she was close by the way her walls contracted around him, making it nearly impossible for him to move. He felt a tightness in his lower back and his knees felt a little weak.

"Shiiit", he groaned when she started to push forward, trying to meet his thrusts. He felt himself about to explode, so he began to pick up his pace slightly. Within seconds, she let out a loud, guttural moan, her fingernails digging into his arms as her body began to shake from her orgasm. Her walls trapped him tight and with a few more pumps, he was releasing a loud growl, reaching a climax of his own.

* * *

Chests heave, hearts race and eyes scan the walls and popcorn ceiling, searching for a sign that this was real life and neither of them were dreaming. After a few moments of attempting to catch their breaths, their roaming eyes somehow land in one another's line of vision, allowing them to make eye contact for the first time since before they did the deed.

Olivia gazes into his usually baby blue pools, which has mysteriously taken on a shade of gray, resembling the aftermath of a storm. Fitz gazes into her warm chocolate orbs and he swears he sees little speckles of gold. Both crack a quick smile as Fitz extracts himself from her, pulling off the condom and throwing it into the trash bin she had placed by the foot of the bed earlier. As he bunches the sheets around his waist and rolls over to lay next to her on his back, he hears her hysterical laughter fill the room. He temporarily feels a shot through his pride, assuming that she was unsatisfied.

"Wow!", she says after finally handling her random fit of laughter. "That was just... wow!"

"Wow?", he asks, turning his head in her direction, using his arm to wipe the sweat away from his forehead.

"Yes, wow!", she turned her head to face him. "Fitz, that was crazy... amazing... just wow!", she exclaims with her eyes widening.

"Yeah?", he smiles, his confidence in full effect.

"Seriously! It's never EVER been that good before. Like EVER!"

"Well you're not too bad yourself either Liv." In all honesty, she was the greatest sex he'd ever had, mostly because either he or whichever girl he happened to bring home had been too drunk to actually enjoy themselves. Not only was he amazed by her tightness, but the way her body responded to him was unbelievable. To know that he was her best sexual encounter, especially after hearing numerous stories over the years, meant something to him in a weird kind of way. But honestly, there was nothing normal about this situation at all.

Olivia couldn't believe how mind blowing having sex with Fitz could be. Not only was he the biggest she had ever encountered, he was also the first to not come before her. Yeah, she had lost the first round, meaning that he would be the one to choose their next position, but in the end it was worth it. She blamed his size and the ability for him to hit her spot with every thrust because of their position for why she was unable to hold out much longer. Olivia knew she had to get back on her game because she had a few positions in mind, especially if she was gonna enjoy herself.

"Whatever dummy. Let's hit the shower and clean ourselves up. That ice cream is calling my name and you promised me take out. Living room in thirty?"

"Pizza should be here by then.."

* * *

**AN: So the feedback I've been getting for this story is amazing! I honestly love this story and love where I see it going. You guys' suggestions have me thinking of switching it all up a bit. Honestly, you guys are great lol! So I was trying to figure out how to incorporate the actual positions into the story and I've decided to do it the way it was shown in this chapter. It's honestly a toss up between putting the whole description before the chapter, which kind of takes away the element of surprise, or within the story, which kind of gives you a visual. Idk, you guys can definitely let me know what you prefer. AND don't be afraid to give your own position suggestions. Seriously, I wanna see what you guys have and if any of you are better than Cosmo lol! This was called The Rock & Roll and I copied the instructions from Cosmos site. Since we can't post links, I'll tell you that I just Googled "cosmo sex" and the first link should take you to their whole Kama Sutra section. I found this position under "Missionary Sex Positions". I encourage everyone to explore! Hope you all enjoyed (:**


End file.
